The answer to that question could go a long way toward understanding a man who ranks third all-time in managerial victories, who will likely pass Hall of Famer John McGraw next season to trail only the legendary Connie Mack, who this week is aiming to become the ninth manager in Major League Baseball history with at least three World Series titles.
For years, La Russa has surrounded himself with excellence. His professional rat pack includes coaching luminaries such as Knight, Parcells, Belichick and Dallas Mavericks boss Rick Carlisle; pop culture icons including Styx frontman Dennis DeYoung, crooner Bruce Hornsby and author John Grisham; and military legend Gen. Hal Moore. Many of them regularly visit La Russa during Spring Training to swap stories and compare notes. Dinner parties are not uncommon.
To some extent, the relationships are a product of mutual fame. But they are hardly coincidence. Baseball managers are often exposed to celebrities, smiling and guffawing and parting ways with a handshake. La Russa is unique in that he seeks to cultivate his new relationships into friendships.
Actor Billy Bob Thornton recalls first meeting La Russa while preparing to throw a ceremonial first pitch during a Spring Training game in 1998. In addition to arranging to have Thornton's childhood hero, Bob Gibson, catch the pitch, La Russa made a point to keep in touch with Thornton over the years. The actor's band has since played at several of La Russa's Animal Rescue Foundation events, and Thornton spoke at a roast for La Russa last winter in St. Louis.
Before beginning his speech, Thornton asked the audience for a 10-second moment of silence. "That was in honor of TLR's personality," he quipped.
But that relationship, like so many of La Russa's friendships, is hardly one-sided. Just as Thornton asks the manager to explain various baseball decisions, so does La Russa pester the actor about the intricacies of Hollywood.
"He'll ask me about certain technical aspects of movie-making the way I ask him about pinch-hitting situations," Thornton said. "I'd hang out with him even if he wasn't a baseball manager. I'd hang out with him if he was a plumber."
La Russa would also hang out with Thornton if he were a plumber -- provided he were a plumber looking to redefine drainage or develop a new type of hydraulic pump. Such forward thinking, more than anything, is what La Russa seeks to gain from his celebrity friendships.
Among the manager's frequent spring dinner guests, for example, is Havlicek, most famous for the steal that helped the Boston Celtics clinch the NBA's 1965 Eastern Conference Championship over the Philadelphia 76ers. Invariably, La Russa will ask Havlicek to detail his memories of that play, from coach Red Auerbach's instructions to his own execution.
"For newcomers, he always wants me to tell the story," Havlicek said. "I think he's always looking for a thought process that may be able to help him in baseball. I tell a story about stealing the ball and how you're always looking for an edge, and he thinks that's pretty neat."
The influence goes both ways, with many of La Russa's celebrity friends grilling him on baseball strategy, from in-game moves to general philosophy. Just as La Russa displays interest in the finer points of zone defense, his friends seek explanation on sacrifice bunts and bullpen machinations.
"When I first met Tony, I thought baseball was basically, you put a dip in between your cheek and gum, you hit some fungoes, say, 'Humm baby,' and that about covers it," former Green Bay Packers general manager Ron Wolf said. "Boy, was I wrong. I was absolutely astonished at the preparation that goes into the season, how much work these guys do, and just how long the season is.
"And Tony, the amount of knowledge he has about the game of baseball is mind-boggling. I pick his brain about it all the time and he's like an encyclopedia. He can recall certain situations from games in the 1980s and '90s and he applies those decisions to how he manages today."
Mostly, though, La Russa's celebrity friends show interest in the man's ability to lead. Without much prompting, it seems, leaders gravitate toward one another.
"As a manager, I think he is remarkable," Parcells said in an email. "His preparation leaves nothing to chance."
It is a preparation that leaks into his personal life. To the extent that he can, La Russa attempts to glean pointers from his celebrity friends and acquaintances, apply them to his own management philosophy and watch the residue stick to his players. It is hardly uncommon behavior -- many professional sports teams employ motivational speakers and former champions to address their players. But La Russa's personal Rolodex runs deepest.
"You notice why people get to be great," Cardinals pitcher Adam Wainwright said. "They all have traits that make them great. And Tony has a little bit of all of them in him."
Asked to reflect on his personal circle of friends and luminaries, La Russa described an attraction to a specific type of person -- always hungry, rarely satisfied, constantly searching for a particular edge or a new line of thinking. He referenced one of his own players, Albert Pujols, as the prototype of a person who does not decelerate upon reaching a plateau.
"The people I've been around, they really enjoy the pursuit," La Russa said. "They take it personal when they're not measuring up."
Relentlessness is a common trait amongst all of them. There is Belichick, the innovative football coach with three Super Bowl titles. There is Carlisle, head of the NBA's reigning champions. There is Parcells, who left comfortable situations multiple times in his career to pursue greater challenges.
There is also Grisham, who once took a break from writing massively successful law thrillers to try his hand at a novel about football. There is DeYoung, who left Styx to pursue solo careers in music and acting. There is Moore, who spent his retirement from the military as a ski resort executive and best-selling author.
And then there is La Russa, one of the winningest managers in baseball history, one of the few men who has adapted successfully to multiple eras of the same game.
"You're talking about a guy that is second all-time in a sport that is older than all those other sports," Wainwright said. "He's about as big time as it gets. So when those guys come in, he's the big-timer."
Moore recalled meeting La Russa for the first time and realizing immediately that he was "a great leader." Few could dispute it, considering the traits that have led La Russa here to Texas this week, with his Cardinals pursuing another World Series title against the Rangers.
Throughout the past month, most around baseball have lauded La Russa for a series of bold strategic moves that, for the most part, have worked in his favor. Spurning orthodoxy, La Russa has routinely removed his best players from the middle innings of games, looking to press small advantages in the areas of baserunning and defense. He has squeezed all he can out of platoon splits and ballpark factors. He has shuffled his roster to gain various edges.
And he has won. Much as he did in 2006, La Russa has taken an overlooked team to the brink of a championship, relying on philosophies and ideas honed over countless hours of debate and discussion.
Nor is he doing this alone. If he wins or if he loses, his friends will be watching.
"He likes to hear stories from all the different walks of life, whether it be music or a Broadway play or a football player or a basketball player or a coach," Havlicek said. "And that's why he has a lot of those people around, because they enjoy him and he enjoys them. It's a great fraternity."